Midterm 2 Flashcards
How many carbons do monosaccharides range between?
3 to 8 carbons
Most common number of carbons in monosaccharides?
Hexoses - 6 carbons
Pentoses - 5 carbons
What is an Aldose?
Carbonyl at the end of the carbon chain
What is a Ketose?
Carbonyl at any location or elsewhere
What are chiral centers?
Carbons with four different substituents
What do chiral centers partly determine?
the type of monossacharide
What are the two types of chiral centers?
Epimers
Enantiomers
What are Epimers?
Monosaccharides that only differ in configuration at one chiral center
What are examples of Epimers?
glucose and mannose
What are Enantiomers?
Monosaccharides that differ in configurations at all chiral centers
What are examples of Enantiomers?
D- and L- glucose
Most carbohydrates in living organisms are _____________.
D- isomers
What structure do most monosaccharides have?
Cyclical structure
— ≥ 4 Carbons have cyclical structure
— they are not written as straight chains
In monosaccharides, what are the two forms of anomers
ß anomer (beta)
∂ anomer (alpha)
What are ß anomers?
-OH of anomeric carbonyl C up
- same side as C-6
What are ∂ anomers?
-OH of anomeric carbonyl D down
- Opposite side from C-6
Why learn about ∂ vs. ß anomers?
Anomeric configuration determines structural properties.
—— Example:
- Starch (good for eating) = contains ∂- glucose
- Cellulose (good for wearing) = contains ß - glucose
What is Pyranose?
5 carbons + 1 oxygen ring
Example: glucopyranose (glucose)
What is Furanose?
4 carbons + 1 oxygen in ring
Example: fructofuranose (fructose)
What structure do most monosaccharides have?
Cyclical structure
— ≥ 4 Carbons have a cyclical structure
— they are not written as straight chains
Since some monosaccharides are reducing sugars, What are reducing sugars?
- Easily reduce copper ions and other compounds
- Sugar is itself oxidized during the process - The site of oxidation is the anomeric carbon (carbonyl)
- Oxizided to carboxyl
+ Example: glucose (carbon 1)
Why are reducing sugars introduced or important?
- They are important for detecting sugars + historically in detecting diabetes.
- in detecting sugars, an oxidizing agent that turns color when reduced
- Common agent: 3,5 dinitrosalicylic agent (easy way to detect glucose in the sample)
— old way of detecting diabetes would be Drs. tasting urine
Monosaccharides have many derivatives, what are the four derivatives talked about in class?
- Amino Sugars (-OH to -NH2)
- Deoxy Sugars (-OH to -H)
- Acidic Sugars (-CH2OH to -COO-)
- Sugar Phosphates (-OH to -OPO3^2-)
What are the building blocks for more complex carbohydrates?
Monosaccharides
Simple Sugar
Monosaccharide
2 Monosaccharides
Disaccharides
Oligosaccharides
3 to ~9 monosaccharides
Many monosaccharides (~10 or more)
Polysaccharides
How are Disaccharides formed?
Formed when anomeric carbon of one monosaccharide is linked with another monosaccharide
What is the linkage called in forming a disaccharide?
glycosidic bond
Example: condensation reaction (forming water)
What are the Common Disaccharides?
- Maltose (from starch)
- Lactose (from milk sugar)
- Sucrose (from photosynthesis) - storage in plants
- Cellobiose (from cellulose)
How are glycosidic bonds named?
- position of carbons involved
- anomeric configuration of the carbons
Example: Glc (∂1–>4) Glc
What is the glycosidic bond of Maltose
Glc (∂1–>4) Glcq
What is the glycosidic bond of Cellobiose?
Glc (ß1–>4) Glc
What is the glycosidic bond of Sucrose?
Glc (∂1 <–>ß2) Fru
What is the glycosidic bond of Lactose?
Gal (ß 1—> 4) Glc
What kind of arrow would it be if there are 2 anomeric carbons?
<––>
What kind of arrow would it be if there is 1 anomeric carbon?
––>
What is a reducing end?
- End of a disaccharide with a free anomeric carbon
- Detectable with DNS or oxidizing agent
- It is not present in all disaccharides
What is an example of a reducing end?
Sucrose
- Resistance to oxidation makes sucrose good storage compound in plants
Why are polysaccharides important biomolecules?
Location of most carbohydrates in organisms
What is the most abundant biomolecule on Earth?
Cellulose
What is the second most abundant biomolecule on Earth?
Chitin
Since polysaccharides take on many forms, What are the structural classes?
- Homopolysaccharides
- Heteropolysaccharides
- Branched
- Unbranched
What type of structural class of polysaccharide is made out of single monosaccharides?
- Simplest and made out of a straight chain
Homopolysaccharides
What type of structural class of polysaccharide is made out of different monosaccharides?
Heteropolysaccharides
What type of structural class of polysaccharide is made out of single monosaccharides?
Homopolysaccharides
What type of structural class of polysaccharide is made out of either homo/hetero-polysaccharides that are branched?
Branched
What type of structural class of polysaccharide is made out of either homo/hetero-polysaccharides that are in a straight chain?
Unbranched
What are examples of polysaccharides that are used for storage?
- Starch, Glycogen and Fructan
What are the two components of starch?
Amylose - unbranched Glc(∂1–>4) Glc
(homopolysaccharides)
Amylopectin - Glc(∂1–>6) Glc branches every 24 to 30 residues
- similar to amylose
-branched polysaccharide
What is Corn Starch made out of?
24% amylose and 76% amylopectin
Where is starch found?
Found in plant endosperm
– seed tissue containing starch granules in grains
– protein matrix surround starch granule
Glycogen is ……
- similar structure ti amylopectin but more frequent branching (every 8 to 12 residues)
- found in animal liver and muscle
- also found in microbes
Why store glucose in polysaccharides?
- Protects cells from high osmolarity
- Glycogen in human liver
- if hydrolyzed, it would form concentrated (0.4M) glucose solution and it would burst the cell
Fructan is …..
Fru (ß2–>6) Fru and Fru (ß2–>1) Fru
Found in plants
Slightly to highly soluble
Up to 30% of grass dry weight — good source of carbs for herbivores
What are examples of polysaccharides that are used in structural forms?
Cellulose, Hemicellulose, Pectin,ß- glucan, Chitin, Peptidoglycan, and Agarose
Cellulose have the following characteristics
- Unbranched Glc(ß1–> 4)Glc
—- identical to amylose, except the ß linkage - Tough, insoluble and indigestible
- Found in cotton, plant cell wall (with other polysaccharides
What are the components of the plant cell wall?
- cellulose
- pectin
- hemicellulose
- ß- glucan
Hemicellulose has…..
- Xylose core: Xyl(ß1–>4)Xyl
- Branches that include arabinose and other sugars
—- similar to glucose + branched heteropolysaccharide
Pectin has…….
- Galacturonic acid core: GalA (∂1–>4) GalA
- Branched that include arabinose, galactose and other sugars
ß-glucan……..
- Glc(ß1–>4)Glc CORE with Glc(ß1–>3)Glc
- Found in plants and microbes
Plant cell wall is
- Indigestible by mammalian enzymes
- Digested by Gastrointestinal microbes (bacteria in cows rumen) and some arthropods
Chitin
- Unbranched N-acetylglucosamine: GlcNAc(ß1–>4) GlcNAc
- found in exoskeletons of arthopods
- second most abundant biomolecule on Earth (after cellulose)
Peptidoglycan
- Unbranched N-acetylglucosamine and acetylmuramic acid: GlcNAc(ß1–>4) Mur2Ac
- contains (crosslinked to) peptide side chain
-found in cell wall of bacteria - broken down by lysozyme (in human tears = antibacterial)
Agarose
- Make up of D- galactose and an L-galactose derivative
- contains charged groups (sulfates and pyruvate)
- red algae
- used in gel electrophoresis
“Other” functional class of polysaccharides
glycosaminoglycans
What are Glycosaminoglycans?
-Polysaccharides from the extracellular matrix of animals
(extracellular matrix =space between cells)
- made of alternating acidic and amino sugars
- some contain charged groups (sulfates), forcing an extended configuration
Example: chondroitin sulfate
- do not exist in free form
- they are attached to proteins to form proteoglycans
Role of glycosaminoglycans in cells
Adhesion
Recognition
signaling
_____________ are covalently attached to glycoproteins
Oligosaccharides
Oligosaccharides are
- rare, except when attached to proteins
- Glycosylation = attachment
- proteins forms are glycoproteins
—> common in mammals = 50% of total proteins
What are glycoproteins?
- oligosaccharides that are short and highly branched
- acetylated residues (e.g., N-acetylglucosamine) common
- Carbohydrate - protein linkages involves the following:
—> Sef/Thr or Asn on protein
—> O- or N- on oligosaccharide
Examples of glycoproteins
Mucin
- component of mucus
- hold water and form gels
Glycoproteins are recognized by
- viruses
- toxins
- bacteria
- other mammalian cells (leukocytes)
!!! important to virulence and immunity
Lipids are __________
structurally diverse
What the definition of a lipid
- Biomolecules that are soluble in organic solvents.
= ether, benzene, chloroform - no other shared feature
What are the two classifications of lipids
- lipids that contain fatty acids
- lipids that do not contain fatty acods
What are examples of lipids that DO have fatty acids?
- Fatty acids
- Triacylglycerols
- Waxes
- Membrane lipids
What are examples of lipids that DO NOT contain fatty acids?
- Sterols
- Fat soluble vitamins
- Pigments
- Polyketides
What is the major class of lipid?
Fatty acid
Fatty acid is made of?
Carboxylic acids with hydrocarbon chains between 4 to 36 carbons
- Saturated = no double bonds
- Unsaturated = one or more double bonds
Nomenclature (lipid number)
- Palmitic acid
- Oleic acid
Palmitic acid has (16:0)
(16:0) = 16 carbons with 0 double bonds
Oleic acid
(18:1 cis -9) = 18 carbons with 1 double bond in cis configuration beginning at carbon 9
Omega 3
- double bond at 3rd carbon from end of the chain
how to write the lipid number
- lipid number could be written as 18:3(n-3)
- could also be written as 18:3 all cis-9,12,15
An example of an Omega 3 is required in the diet
- ∂-linolenic acid
- Eicosapentaenoic acid (EPA)
- Docosahexaenoic acid (DHA)
∂- linolenic acid
cannot be synthesized
- animals lack desaturase enzymes to form the unsaturated bonds
Eicosapentaenoic acid (EPA) (20:5 n-3)
- can be synthesized from ∂-linolenic acid to form the unsaturated bonds
- otherwise required in diet